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Showing NP-Card for [4-(prop-1-en-2-yl)cyclohexyl]methanol (NP0327811)

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Record Information
Version2.0
Created at2022-09-12 10:43:50 UTC
Updated at2022-09-12 10:43:50 UTC
NP-MRD IDNP0327811
Secondary Accession NumbersNone
Natural Product Identification
Common Name[4-(prop-1-en-2-yl)cyclohexyl]methanol
DescriptionCis-Isopulegone belongs to the class of organic compounds known as menthane monoterpenoids. These are monoterpenoids with a structure based on the o-, m-, or p-menthane backbone. P-menthane consists of the cyclohexane ring with a methyl group and a (2-methyl)-propyl group at the 1 and 4 ring position, respectively. The o- and m- menthanes are much rarer, and presumably arise by alkyl migration of p-menthanes. Cis-Isopulegone is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, cis-Isopulegone has been detected, but not quantified in, fats and oils. [4-(prop-1-en-2-yl)cyclohexyl]methanol is found in Agathosma betulina. This could make cis-isopulegone a potential biomarker for the consumption of these foods.
Structure
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MOL3D MOLSDFPDBSMILESInChI

MOL for NP0327811 ([4-(prop-1-en-2-yl)cyclohexyl]methanol)

Perillyl aldehyde metabolite 2
  Mrv1572001071617222D          

 11 11  0  0  0  0            999 V2000
    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7144   -2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 10  1  1  6  0  0  0
  8  4  1  6  0  0  0
  8  7  2  0  0  0  0
  9  8  1  0  0  0  0
  6  5  1  0  0  0  0
  6  1  1  0  0  0  0
  3  2  1  0  0  0  0
  5  4  1  0  0  0  0
  4  3  1  0  0  0  0
 10 11  1  0  0  0  0
  2  1  1  0  0  0  0
M  END
Download

3D MOL for NP0327811 ([4-(prop-1-en-2-yl)cyclohexyl]methanol)

     RDKit          3D

 29 29  0  0  0  0  0  0  0  0999 V2000
   -3.1071   -0.8468    0.0605 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2039    0.0726    0.1643 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6484    1.5167    0.1367 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7484   -0.1167    0.3108 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.0968    0.6412   -0.8282 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1515   -0.0540   -1.3091 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9629   -0.5938   -0.1641 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.5589    0.5850    0.5799 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3790    1.3461   -0.2463 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1861   -1.4886    0.7555 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2901   -1.5305    0.3401 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1389   -0.5851   -0.0419 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8295   -1.8854    0.0759 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6539    1.5894    0.6218 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9687    2.1573    0.7332 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6448    1.8736   -0.9051 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4661    0.3467    1.2984 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1133    1.6714   -0.4578 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7809    0.7113   -1.7056 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8202   -0.8803   -1.9836 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7704    0.6410   -1.8787 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8425   -1.1272   -0.6289 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7491    1.2460    0.9464 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1542    0.2213    1.4587 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0877    2.2908   -0.3214 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6359   -2.5176    0.7016 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2875   -1.1265    1.8010 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8043   -2.1099    1.1094 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3171   -2.0482   -0.6235 H   0  0  0  0  0  0  0  0  0  0  0  0
  3  2  1  0
  2  1  2  3
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  7 10  1  0
 10 11  1  0
 11  4  1  0
  3 14  1  0
  3 15  1  0
  3 16  1  0
  1 12  1  0
  1 13  1  0
  4 17  1  1
  5 18  1  0
  5 19  1  0
  6 20  1  0
  6 21  1  0
  7 22  1  6
  8 23  1  0
  8 24  1  0
  9 25  1  0
 10 26  1  0
 10 27  1  0
 11 28  1  0
 11 29  1  0
M  END
Download

3D SDF for NP0327811 ([4-(prop-1-en-2-yl)cyclohexyl]methanol)

Perillyl aldehyde metabolite 2
  Mrv1572001071617222D          

 11 11  0  0  0  0            999 V2000
    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7144   -2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 10  1  1  6  0  0  0
  8  4  1  6  0  0  0
  8  7  2  0  0  0  0
  9  8  1  0  0  0  0
  6  5  1  0  0  0  0
  6  1  1  0  0  0  0
  3  2  1  0  0  0  0
  5  4  1  0  0  0  0
  4  3  1  0  0  0  0
 10 11  1  0  0  0  0
  2  1  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0327811

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(=C)C1CCC(CO)CC1

> <INCHI_IDENTIFIER>
InChI=1S/C10H18O/c1-8(2)10-5-3-9(7-11)4-6-10/h9-11H,1,3-7H2,2H3

> <INCHI_KEY>
GMYHXOPIKMGWOM-UHFFFAOYSA-N

> <FORMULA>
C10H18O

> <MOLECULAR_WEIGHT>
154.253

> <EXACT_MASS>
154.1357652

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_ATOM_COUNT>
29

> <JCHEM_AVERAGE_POLARIZABILITY>
19.177734007344892

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
[4-(prop-1-en-2-yl)cyclohexyl]methanol

> <ALOGPS_LOGP>
2.88

> <JCHEM_LOGP>
2.2666672463333337

> <ALOGPS_LOGS>
-2.36

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
17.643040612403414

> <JCHEM_PKA_STRONGEST_BASIC>
-1.6427340361347467

> <JCHEM_POLAR_SURFACE_AREA>
20.23

> <JCHEM_REFRACTIVITY>
47.482

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
6.76e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
[4-(prop-1-en-2-yl)cyclohexyl]methanol

> <JCHEM_VEBER_RULE>
1

$$$$
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3D-SDF for NP0327811 ([4-(prop-1-en-2-yl)cyclohexyl]methanol)

Download
PDB for NP0327811 ([4-(prop-1-en-2-yl)cyclohexyl]methanol)
HEADER    PROTEIN                                 07-JAN-16   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: Perillyl aldehyde metabolite 2                    
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   07-JAN-16         0                                  
HETATM    1  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.334   0.770   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.000  -1.540   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -1.334   0.770   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -1.334  -3.850   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.000  -3.080   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.334  -3.850   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.000   3.080   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       1.334   3.850   0.000  0.00  0.00           O+0
CONECT    1   10    6    2                                                  
CONECT    2    3    1                                                       
CONECT    3    2    4                                                       
CONECT    4    8    5    3                                                  
CONECT    5    6    4                                                       
CONECT    6    5    1                                                       
CONECT    7    8                                                            
CONECT    8    4    7    9                                                  
CONECT    9    8                                                            
CONECT   10    1   11                                                       
CONECT   11   10                                                            
MASTER        0    0    0    0    0    0    0    0   11    0   22    0
END

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3D PDB for NP0327811 ([4-(prop-1-en-2-yl)cyclohexyl]methanol)
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SMILES for NP0327811 ([4-(prop-1-en-2-yl)cyclohexyl]methanol)
CC(=C)C1CCC(CO)CC1
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INCHI for NP0327811 ([4-(prop-1-en-2-yl)cyclohexyl]methanol)
InChI=1S/C10H18O/c1-8(2)10-5-3-9(7-11)4-6-10/h9-11H,1,3-7H2,2H3
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View in JSmol
Synonyms
ValueSource
cis-p-Menth-8-en-7-olHMDB
PulegoneMeSH
cis-IsopulegoneMeSH
Pulegone, (S)-isomerMeSH
IsopulegoneMeSH
Pulegone, (R)-isomerMeSH
Chemical FormulaC10H18O
Average Mass154.2530 Da
Monoisotopic Mass154.13577 Da
IUPAC Name[4-(prop-1-en-2-yl)cyclohexyl]methanol
Traditional Name[4-(prop-1-en-2-yl)cyclohexyl]methanol
CAS Registry NumberNot Available
SMILES
CC(=C)C1CCC(CO)CC1
InChI Identifier
InChI=1S/C10H18O/c1-8(2)10-5-3-9(7-11)4-6-10/h9-11H,1,3-7H2,2H3
InChI KeyGMYHXOPIKMGWOM-UHFFFAOYSA-N
Experimental Spectra
Not Available
Predicted Spectra
Spectrum TypeDescriptionDepositor IDDepositor OrganizationDepositorDeposition DateView
1D NMR13C NMR Spectrum (1D, 25 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 252 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 50 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 75 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 101 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 126 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 151 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 176 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 201 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 226 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Agathosma betulinaLOTUS Database
Chemical Taxonomy
Description Belongs to the class of organic compounds known as menthane monoterpenoids. These are monoterpenoids with a structure based on the o-, m-, or p-menthane backbone. P-menthane consists of the cyclohexane ring with a methyl group and a (2-methyl)-propyl group at the 1 and 4 ring position, respectively. The o- and m- menthanes are much rarer, and presumably arise by alkyl migration of p-menthanes.
KingdomOrganic compounds  
Super ClassLipids and lipid-like molecules  
ClassPrenol lipids  
Sub ClassMonoterpenoids  
Direct ParentMenthane monoterpenoids  
Alternative Parents
Substituents
  • P-menthane monoterpenoid
    • 

  • Monocyclic monoterpenoid
    • 

  • Organic oxygen compound
    • 

  • Hydrocarbon derivative
    • 

  • Primary alcohol
    • 

  • Organooxygen compound
    • 

  • Alcohol
    • 

  • Aliphatic homomonocyclic compound
Molecular FrameworkAliphatic homomonocyclic compounds
External DescriptorsNot Available
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP2.88ALOGPS
logP2.27ChemAxon
logS-2.4ALOGPS
pKa (Strongest Acidic)17.64ChemAxon
pKa (Strongest Basic)-1.6ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area20.23 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity47.48 m³·mol⁻¹ChemAxon
Polarizability19.18 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0037006  
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB015981  
KNApSAcK IDNot Available
Chemspider ID453538  
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound519954  
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. LOTUS database [Link]